Its the nature of this business.

[Natural disaster, huge sinkhole where earth swallows it all up, etc] - insurance?

I followed the link Account Closed posted and based on my natural pettiness would be likely to pay the $30 even though I think collection probability would be low just so when their credit is pulled there is a clear scarlet letter warning future landlords this person is a deadbeat.  

Encroachment of this nature should not impede your ability to sell in securing lending for your future buyer. 

You're a nice landlord with a heart and it shows for second guessing yourself, but you will grow tough skin over time ;)Best of luck to you!

Human nature at work.

@Eric B. most of HML would require the investor to have skin in the game, only lend portion of the price (75-90%).

And naturally quit my job the next day..

Instead of a cheaper natural gas furnace you are going to be paying the electric on the space heaters.

They have no skin in the game after the house closes, the insurer does.I would highly suggest, with the condition you suggest the roof is in (5-8 years left on a shingle might as well be 0 with a preferred underwriter), that you look at Foremost, Berkshire Hathaway, and or USLI.